The 1993 song Kool Keith considers the best rap song of all time
Kool Keith is one of rap’s eccentrics, a man with an expansive imagination and a sharp, if sometimes odd, sense of humour.
His music, even when it’s at its horrorcore extremes, leaves space for a chuckle, and his personal taste in rap music is similarly drawn towards the funny.
Speaking to Pitchfork in 2023 for a piece celebrating a half-century of hip hop culture, he mentioned what his favourite rap song of all time was, and it was one capable of eliciting a laugh, at least from his perspective.
Released as part of his The Mail Man EP in 1993, ‘Captain Save a Hoe’ was E-40’s breakout hit, which tells the tale of a man who seeks to impress the opposite sex by spending lots of his time and money on them. He is mocked for doing so, depicted ironically as a superhero-like figure, “Captain Save a Hoe”.
E-40 once explained to Complex in 2011 that the Captain Save a Hoe character wants to “save” a promiscuous woman and to “turn her into a housewife”. He is “the type of dude buying her clothes, cars, whatever he can do”, going out of his way to impress this woman and, ultimately, to tame her.
The song has been criticised from a feminist perspective, as it seems to depict women as gold-diggers leveraging their sexuality for the sake of exploiting the little money a Black man might earn. There are, clearly, parts of the song that veer into sexism, but on the other hand, the Captain Save a Hoe figure is definitely not being celebrated for his ways and being mocked for his attitudes and actions.
Regardless of one’s own thoughts about the song’s perspective, one person who absolutely loves it is Kool Keith, who was full of praise for its maker, saying, “E-40 is so naturally funny and clever. He’s a break from the average rapper”.
Coming from a figure as off-kilter as Kool Keith, that is a huge compliment. He admired E-40’s “rhythmic tricks and vocal acrobatics”, which he felt distinguished him from most other rappers. “He’s kind of like myself,” Keith said, “You can’t duplicate his songs”.
While some listeners might recoil a bit from the more sexist tendencies of ‘Captain Save a Hoe’, Keith considers it “a pimp song, but not in a bad way; straight entertaining instead of downgrading”, because it’s humorous, and ultimately, it doesn’t take Captain Save a Hoe’s side. Keith was also hugely fond of the track’s West Coast, synth-heavy feel, adding, “It’s soulful. Music for a day riding around in Oakland, hitting a bar, and hanging with people who are real”.